[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

JP2010539262A - High concentration fatty alcohol sulfate preparation - Google Patents

High concentration fatty alcohol sulfate preparation Download PDF

Info

Publication number
JP2010539262A
JP2010539262A JP2010524384A JP2010524384A JP2010539262A JP 2010539262 A JP2010539262 A JP 2010539262A JP 2010524384 A JP2010524384 A JP 2010524384A JP 2010524384 A JP2010524384 A JP 2010524384A JP 2010539262 A JP2010539262 A JP 2010539262A
Authority
JP
Japan
Prior art keywords
weight
composition
fatty alcohol
alkyl sulfate
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP2010524384A
Other languages
Japanese (ja)
Other versions
JP5854605B2 (en
Inventor
ローラント・シュペーラー
スララト・ジャリヤチャト
テディ・ワウォルンツ
アフマド・ジャズリ
アフマド・タウフィク
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Publication of JP2010539262A publication Critical patent/JP2010539262A/en
Application granted granted Critical
Publication of JP5854605B2 publication Critical patent/JP5854605B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2044—Dihydric alcohols linear
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2065—Polyhydric alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/521—Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本発明は、３５重量％超の脂肪アルコールスルフェート（ＦＡＳ）を含んでなる濃厚脂肪アルコールスルフェート製剤に関する。該製剤は水を含むが、ＦＡＳに加えてポリオールまたは油溶性ベタインも含む。該製剤は、洗剤および洗浄剤の製造に適しているが、化粧品、特にデンタルケア製品の製造にも適している。The present invention relates to a concentrated fatty alcohol sulfate formulation comprising more than 35% by weight of fatty alcohol sulfate (FAS). The formulation contains water but also contains polyol or oil-soluble betaine in addition to FAS. The formulations are suitable for the production of detergents and cleaning agents, but are also suitable for the production of cosmetics, in particular dental care products.

Description

本特許出願は、アルキルスルフェート界面活性剤に基づく濃厚界面活性製剤、その使用、およびその製造方法に関する。   The present patent application relates to concentrated surfactant formulations based on alkyl sulfate surfactants, their use, and methods for their production.

脂肪アルコールスルフェートは、多数の洗剤および洗浄剤だけでなく化粧品、例えば、シャンプー、皮膚洗浄組成物、皮膚用石鹸および練り歯磨きにも使用される、既知のアニオン性界面活性剤である。   Fatty alcohol sulfates are known anionic surfactants used in cosmetics such as shampoos, skin cleansing compositions, skin soaps and toothpastes as well as numerous detergents and cleansers.

アルキルスルフェートは、一般に、適当な脂肪アルコールをＳＯ３ガスで硫酸化することによって工業的に製造される。その過程で粗生成物として生じるアルキル硫酸を、その後、適当なアルカリ、好ましくは水酸化ナトリウム水溶液の存在下で中和し、アルキルスルフェートを得る。そのような方法の終わりに、最大３０重量％のアニオン性界面活性剤を含む界面活性剤含有水性製剤を得る。 Alkyl sulfates are generally produced industrially by sulfating a suitable fatty alcohol with SO 3 gas. The alkyl sulfuric acid produced as a crude product in the process is then neutralized in the presence of a suitable alkali, preferably an aqueous sodium hydroxide solution, to obtain the alkyl sulfate. At the end of such a process, a surfactant-containing aqueous formulation comprising up to 30% by weight of an anionic surfactant is obtained.

そのような製剤を輸送するため、輸送がより容易になる乾燥生成物を得る目的で、水がしばしば除去される。しかしながら、水の除去は、多くのエネルギーを消費し、従って高価である、工程段階を構成する。直接製造された水性組成物自体を輸送することは有利ではない。そうすることで、僅かな比較的少量の活性物質（最大３０重量％）および多量の水が輸送される。更に、乾燥脂肪アルコールスルフェートの配合には時間を要する。液状脂肪アルコールスルフェートの使用は一般に、シャンプー、皮膚洗浄組成物、皮膚用石鹸、および練り歯磨きのメーカー側に、２０％を超えるバッチ時間短縮をもたらす。   In order to transport such formulations, water is often removed in order to obtain a dry product that is easier to transport. However, water removal constitutes a process step that consumes a lot of energy and is therefore expensive. It is not advantageous to transport the directly produced aqueous composition itself. By doing so, only a relatively small amount of active substance (up to 30% by weight) and a large amount of water are transported. Furthermore, it takes time to formulate the dry fatty alcohol sulfate. The use of liquid fatty alcohol sulfate generally results in a batch time reduction of over 20% on the shampoo, skin cleansing composition, skin soap, and toothpaste manufacturer side.

従って、前記問題を回避するために、ポンプ輸送可能な、液状または若干ペースト状である高濃度脂肪アルコールスルフェート製剤を提供する要求が存在する。   Accordingly, there is a need to provide a high concentration fatty alcohol sulfate formulation that is pumpable, liquid or slightly pasty, to avoid the above problems.

ある種の添加剤を添加することによって、比較的高濃度のポンプ輸送可能な、即ち低粘性の脂肪アルコール製剤が得られることが見出された。   It has been found that by adding certain additives, a relatively high concentration of pumpable, ie low viscosity, fatty alcohol formulation is obtained.

従って、本特許出願はまず、
少なくとも
（ａ）組成物の総重量に基づいて３５重量％の、一般式（Ｉ）：
Ｒ１Ｏ−ＳＯ３Ｘ （Ｉ）
［式中、Ｒ１は、６〜２２個、好ましくは１２〜１８個の炭素原子を有する、直鎖または分枝の脂肪族アルキルおよび／またはアルケニル基であり、Ｘは、アルカリ金属および／またはアルカリ土類金属、アンモニウム、アルキルアンモニウム、アルカノールアンモニウムまたはグルカンモニウムである。］
で示される１種以上の脂肪アルコールスルフェートと、
（ｂ）ポリオール、および／またはベタイン、および／または脂肪酸アルキルアミド、並びに
（ｃ）水
を含んでなる組成物を提供する。 Therefore, this patent application
At least (a) 35% by weight, based on the total weight of the composition, of the general formula (I):
R 1 O—SO 3 X (I)
Wherein R 1 is a straight or branched aliphatic alkyl and / or alkenyl group having 6 to 22, preferably 12 to 18 carbon atoms, X is an alkali metal and / or Alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucanmonium. ]
One or more fatty alcohol sulfates represented by:
Provided is a composition comprising (b) a polyol and / or betaine, and / or a fatty acid alkylamide, and (c) water.

しばしば「脂肪アルコールスルフェート」とも称される、アルキルスルフェートおよび／またはアルケニルスルフェートは、式（Ｉ）：
Ｒ１Ｏ−ＳＯ３Ｘ （Ｉ）
［式中、Ｒ１は、６〜２２個、好ましくは１２〜１８個の炭素原子を有する、直鎖または分枝の脂肪族アルキルおよび／またはアルケニル基であり、Ｘは、アルカリ金属および／またはアルカリ土類金属、アンモニウム、アルキルアンモニウム、アルカノールアンモニウムまたはグルカンモニウムである。］
で示される、第一級アルコールの硫酸化生成物を意味すると理解される。本発明において使用できるアルキルスルフェートの典型的な例は、下記アルコールの硫酸化生成物である：カプロンアルコール、カプリルアルコール、カプリンアルコール、２−エチルヘキシルアルコール、ラウリルアルコール、ミリスチルアルコール、セチルアルコール、パルモレイルアルコール、ステアリルアルコール、イソステアリルアルコール、オレイルアルコール、エライジルアルコール、ペトロセリニルアルコール、アラキルアルコール、ガドレイルアルコール、ベヘニルアルコールおよびエルシルアルコール、並びに工業用メチルエステル画分またはRoelenのオキソ合成由来のアルデヒドを高圧水素化することにより得られるそれらの工業用混合物。硫酸化生成物は、好ましくはアルカリ金属塩、特にナトリウム塩の状態で使用され得る。 Alkyl sulfates and / or alkenyl sulfates, often referred to as “fatty alcohol sulfates”, are of formula (I):
R 1 O—SO 3 X (I)
Wherein R 1 is a straight or branched aliphatic alkyl and / or alkenyl group having 6 to 22, preferably 12 to 18 carbon atoms, X is an alkali metal and / or Alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucanmonium. ]
Is understood to mean the sulfated product of the primary alcohol. Typical examples of alkyl sulfates that can be used in the present invention are the sulfated products of the following alcohols: capron alcohol, capryl alcohol, caprin alcohol, 2-ethylhexyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl. Alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petrocerinyl alcohol, aralkyl alcohol, gadrelyl alcohol, behenyl alcohol and erucyl alcohol, and industrial methyl ester fractions or aldehydes derived from Roelen's oxo synthesis Those industrial mixtures obtained by high-pressure hydrogenation. The sulfated product can preferably be used in the form of alkali metal salts, in particular sodium salts.

ナトリウム塩状態の、Ｃ１６／１８獣脂脂肪アルコールおよび／または同程度の炭素鎖分布の植物性脂肪アルコールに基づくアルキルスルフェートが特に好ましい。ドデシルアルコールに基づくアルキルスルフェートは、デンタルケア組成物およびデンタルクリーニング組成物に使用されるので、特に重要であり得る。しかしながら、１２〜１４個の炭素原子を有する脂肪アルコールからの脂肪アルコールカットが更に好ましく、この場合、例えば脂肪アルコールの量に基づいて、１０重量％未満、好ましくは５重量％未満、特に３重量％未満の、極めて少量のＣ１６脂肪アルコール画分しか含まないカットを使用することが本発明では特に好ましい。更に、飽和脂肪アルコールおよび前記カットが本発明ではとりわけ好ましい。 Particularly preferred are alkyl sulfates based on C 16/18 tallow fatty alcohol in the sodium salt state and / or vegetable fatty alcohols of similar carbon chain distribution. Alkyl sulfates based on dodecyl alcohol can be particularly important as they are used in dental care and dental cleaning compositions. However, fatty alcohol cuts from fatty alcohols having 12 to 14 carbon atoms are more preferred, in which case, for example, based on the amount of fatty alcohol, less than 10% by weight, preferably less than 5% by weight, in particular 3% by weight. It is particularly preferred in the present invention to use cuts that contain less than a very small amount of the C16 fatty alcohol fraction. Furthermore, saturated fatty alcohols and said cuts are particularly preferred in the present invention.

本発明の組成物は、高濃度である、即ち、本特許出願において組成物全体に基づいて少なくとも３５重量％の脂肪アルコールスルフェートを含んでなるといった事実を特徴とする。しかしながら、特許請求されている技術的教示に従った本発明の組成物は、組成物の総重量に基づいて、好ましくは３５重量％超、より好ましくは３６重量％〜７０重量％、特に４０〜６０重量％、特に好ましくは４０〜５０重量％の量で脂肪アルコールスルフェートを含んでなり得る。   The composition according to the invention is characterized by the fact that it is highly concentrated, ie it comprises at least 35% by weight of fatty alcohol sulfate based on the total composition in the patent application. However, the composition according to the invention in accordance with the claimed technical teaching is preferably more than 35% by weight, more preferably 36% to 70% by weight, in particular 40 to 40%, based on the total weight of the composition. It may comprise fatty alcohol sulfate in an amount of 60% by weight, particularly preferably 40-50% by weight.

本発明の本質的特徴は、ポリオール、またはベタインおよび／または脂肪酸アルキルアミドの存在である。ただし、この３つの群のうち、ポリオールが好ましい選択肢である。   An essential feature of the present invention is the presence of a polyol, or betaine and / or a fatty acid alkylamide. Of these three groups, however, polyol is the preferred option.

本発明に適したポリオールは、好ましくは２〜１５個の炭素原子および少なくとも２個のヒドロキシル基を有する。ポリオールは更なる官能基、特にアミノ基を含有することもでき、および／または窒素で変性されていてもよい。典型的な例は以下である：グリセロール；アルキレングリコール、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、ヘキシレングリコール、および１００〜１０００ダルトンの平均分子量を有するポリエチレングリコール；１．５〜１０の自己縮合度を有する工業用オリゴグリセリル混合物、例えば、４０〜５０重量％のジグリセロール濃度を有する工業用ジグリセロール混合物；メチロール化合物、例えば、特に、トリメチロールエタン、トリメチロールプロパン、トリメチロールブタン、ペンタエリスリトールおよびジペンタエリスリトール；低級アルキルグルコシド、特に、アルキル基に１〜８個の炭素原子を有するもの、例えば、メチルグルコシドおよびブチルグルコシド；５〜１２個の炭素原子を有する糖アルコール、例えば、ソルビトールまたはマンニトール；５〜１２個の炭素原子を有する糖、例えば、グルコースまたはスクロース；アミノ糖、例えばグルカミン；ジアルコールアミン、例えば、ジエタノールアミンまたは２−アミノ−１，３−プロパンジオール。好ましいポリオールは、グリセロール、エチレングリコール、プロピレングリコールまたはソルビトールからなる群から選択される。グリセロールおよびソルビトールが特に好ましい。   Polyols suitable for the present invention preferably have 2 to 15 carbon atoms and at least 2 hydroxyl groups. The polyols can also contain further functional groups, in particular amino groups, and / or can be modified with nitrogen. Typical examples are: glycerol; alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycol having an average molecular weight of 100-1000 daltons; Industrial oligoglyceryl mixtures having a degree of self-condensation, for example industrial diglycerol mixtures having a diglycerol concentration of 40 to 50% by weight; methylol compounds such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, penta Erythritol and dipentaerythritol; lower alkyl glucosides, especially those having 1 to 8 carbon atoms in the alkyl group, such as methyl glucoside and butyl glucoside; Sugar alcohols having 2 carbon atoms, such as sorbitol or mannitol; sugars having 5-12 carbon atoms, such as glucose or sucrose; amino sugars, such as glucamine; dialcohol amines, such as diethanolamine or 2-amino -1,3-propanediol. Preferred polyols are selected from the group consisting of glycerol, ethylene glycol, propylene glycol or sorbitol. Glycerol and sorbitol are particularly preferred.

ベタインは、アミン化合物のカルボキシアルキル化、好ましくはカルボキシメチル化によって主に生成される、既知の界面活性剤である。好適には、出発物質を、ハロカルボン酸またはその塩、特にクロロ酢酸ナトリウムと縮合させて、ベタイン１モルにつき塩１モルを生成させる。更に、不飽和カルボン酸、例えばアクリル酸の付加も可能である。油、即ちトリグリセリドの反応によって得られるベタインが特に好ましい。例として、Ｎ，Ｎ−ジメチル−Ｎ−（ココアミドプロピル）アンモニウムアセトベタイン（Dehyton PK 45 - Cognis）を挙げることができる。   Betaine is a known surfactant produced primarily by carboxyalkylation, preferably carboxymethylation, of amine compounds. Preferably, the starting material is condensed with a halocarboxylic acid or salt thereof, in particular sodium chloroacetate, to produce 1 mole of salt per mole of betaine. Furthermore, addition of unsaturated carboxylic acids such as acrylic acid is also possible. Particular preference is given to betaines obtained by reaction of oils, ie triglycerides. As an example, mention may be made of N, N-dimethyl-N- (cocoamidopropyl) ammonium acetobetaine (Dehyton PK 45-Cognis).

油溶性ベタインが好ましい。   Oil soluble betaines are preferred.

脂肪酸アルキルアミドは、同様に、それ自体知られている化合物である。脂肪酸アルキルアミドはまた、狭義には脂肪酸アルカノールアミドを包含すると理解される。脂肪酸ジエタノールアミドまたは脂肪酸モノエタノールアミドが、本発明では特に好ましい。これに関連して、７〜２１個の炭素鎖長さを有する飽和または不飽和、分枝または非分枝の脂肪酸を含んでなる、このタイプの化合物が更に好ましい。それらは、例えば"Comperlan"の名称で本特許出願人よって販売されている。ヤシ脂肪酸モノエタノールアミドに基づく脂肪酸アルキルアミドが特に好ましい。油溶性脂肪酸アルキルアミドが特に好ましいと思われる。   Fatty acid alkylamides are likewise compounds known per se. Fatty acid alkylamides are also understood to encompass fatty acid alkanolamides in a narrow sense. Fatty acid diethanolamide or fatty acid monoethanolamide is particularly preferred in the present invention. In this connection, more preferred are compounds of this type which comprise saturated or unsaturated, branched or unbranched fatty acids having a length of 7 to 21 carbon chains. They are sold, for example, by the present applicant under the name “Comperlan”. Fatty acid alkylamides based on coconut fatty acid monoethanolamide are particularly preferred. Oil soluble fatty acid alkylamides may be particularly preferred.

組成物中にはポリオールだけでなくベタインおよび／または脂肪酸アルキルアミドが、組成物の総重量に基づいて、１０〜４５重量％、好ましくは１５〜４０重量％、特に２５〜３５重量％の量で存在する。ポリオール、ベタインおよび／または脂肪酸アルキルアミドの混合物を使用することが好ましい。   In the composition, not only the polyol but also betaine and / or fatty acid alkylamides in an amount of 10 to 45% by weight, preferably 15 to 40% by weight, in particular 25 to 35% by weight, based on the total weight of the composition. Exists. Preference is given to using mixtures of polyols, betaines and / or fatty acid alkylamides.

本発明の組成物は、脂肪アルコールスルフェート、ポリオールまたはベタインまたは脂肪酸アルキルアミド、および水を必ず含んでなるが、他の成分、例えば無機塩または非イオン性界面活性剤を更に含んでなることもできる。しかしながら、３つの特定成分のみからなる組成物が特に好ましい。   The composition of the present invention necessarily comprises a fatty alcohol sulfate, a polyol or betaine or a fatty acid alkylamide, and water, but may further comprise other components such as inorganic salts or nonionic surfactants. it can. However, a composition consisting of only three specific components is particularly preferred.

水性組成物は、好ましくは８より大きいｐＨを有する。ｐＨは好ましくは９〜１２の範囲であり、特に好ましくは１０〜１２の範囲である。組成物は、液体状態またはペースト状態、好ましくは低粘性のポンプ輸送可能なペースト状態であり得る。２５℃でブルックフィールドに従って測定された典型的な粘度（スピンドル３または４、１０ｒｐｍ）は、５００〜１００００ｍＰａｓ、好ましくは１０００〜８０００ｍＰａｓである。   The aqueous composition preferably has a pH greater than 8. The pH is preferably in the range of 9-12, particularly preferably in the range of 10-12. The composition can be in a liquid state or a paste state, preferably a low viscosity pumpable paste state. Typical viscosities (spindle 3 or 4, 10 rpm) measured according to Brookfield at 25 ° C. are 500-10000 mPas, preferably 1000-8000 mPas.

本発明において好ましい組成物は、組成物全体の重量に基づいて、（ａ）３６〜４５重量％の、式（Ｉ）で示されるアルキルスルフェート、（ｂ）２８〜４５重量％の、ポリオール（ここで、グリセロールおよび／またはソルビトールが好ましい）、またはベタイン、および／または脂肪酸アルキルアミド、（ｃ）１０〜３４重量％の水を含んでなる。   Preferred compositions in the present invention include (a) 36 to 45% by weight of alkyl sulfate of formula (I), (b) 28 to 45% by weight of polyol (based on the total weight of the composition). Where glycerol and / or sorbitol are preferred), or betaine, and / or fatty acid alkylamides, (c) comprising 10 to 34% by weight of water.

濃厚脂肪アルコール製剤は、好ましくは、水／ポリオールまたはベタイン混合物の存在下で硫酸脂肪アルコールエステルを中和することによって製造される。従って、本発明の更なる主題は、一般式：Ｒ１−ＯＳＯ３Ｈで示される未中和アルキルスルフェートを所定量のアルカリと一緒に、（Ａ）水と（Ｂ）ポリオールまたはベタインとの混合物に連続的に添加する、少なくとも３５重量％の式（Ｉ）で示されるアルキルスルフェートを含んでなる前記製剤の製造方法であって、（Ａ）と（Ｂ）との体積比を３：１〜１：３の値に調節し、アルカリの量がアルキルスルフェートを完全に中和するのに適しており、式（Ｉ）で示される中和アルキルスルフェートの濃度が少なくとも３５重量％に達するまで、（Ａ）と（Ｂ）との混合物と、未中和アルキルスルフェートおよびアルカリとの混合を継続する、方法に関する。 The concentrated fatty alcohol formulation is preferably made by neutralizing the sulfated fatty alcohol ester in the presence of a water / polyol or betaine mixture. Accordingly, a further subject of the present invention is a non-neutralized alkyl sulfate of the general formula: R 1 -OSO 3 H together with a certain amount of alkali, with (A) water and (B) a polyol or betaine. A process for the preparation of said formulation comprising at least 35% by weight of an alkyl sulfate of formula (I), which is continuously added to the mixture, wherein the volume ratio of (A) to (B) is 3: Adjusted to a value of 1-1: 3, the amount of alkali is suitable for complete neutralization of the alkyl sulfate, and the concentration of the neutralized alkyl sulfate of formula (I) is at least 35% by weight Until reaching the mixture of (A) and (B) with the unneutralized alkyl sulfate and alkali.

脂肪アルコールの硫酸化は、ＳＯ３を用いて既知の方法で実施される。次いで、粗硫酸化生成物を（Ａ）と（Ｂ）との混合物に計量添加し、加えて、同時の混合および中和が起こるように、アルカリ金属水酸化物水溶液、好ましくは水酸化ナトリウム水溶液を好適には独立して計量添加する。脂肪アルコールスルフェート製剤の所望の濃度範囲に達するまで、この処理を実施する。続いて、所望により、更なる添加剤または成分を計量添加することもできる。その後、プロセス生成物を例えば漂白および／または芳香付けすることもできる。（Ａ）と（Ｂ）との量比を互いに変えることが有利であり得る。ここで、３：１〜１：１、特に２：１〜１．５：１の範囲の体積比がとりわけ好ましい。 The sulfation of fatty alcohols is carried out in a known manner using SO 3 . The crude sulfated product is then metered into the mixture of (A) and (B) and, in addition, an aqueous alkali metal hydroxide solution, preferably an aqueous sodium hydroxide solution, so that simultaneous mixing and neutralization occurs. Are preferably metered independently. This treatment is carried out until the desired concentration range of the fatty alcohol sulfate formulation is reached. Subsequently, further additives or ingredients can be metered in if desired. The process product can then be bleached and / or fragranced, for example. It may be advantageous to change the quantity ratio of (A) and (B) to each other. Here, a volume ratio in the range of 3: 1 to 1: 1, in particular 2: 1 to 1.5: 1, is particularly preferred.

本発明の更なる主題は、洗剤または洗浄剤、或いは化粧品、例えばヘアシャンプーまたは練り歯磨き若しくは類似ケア製品を製造するための、前記組成物の使用に関する。本教示における濃厚アルキルスルフェートを含んでなる、洗剤、洗浄剤および／または化粧品も同様に、保護が求められる発明の主題である。   A further subject matter of the present invention relates to the use of said composition for the manufacture of detergents or cleaning agents, or cosmetics such as hair shampoos or toothpastes or similar care products. Detergents, detergents and / or cosmetics comprising concentrated alkyl sulfates in the present teachings are likewise the subject of the invention for which protection is sought.

Ｃ１２：６５〜７１重量％；Ｃ１４：２２〜２８重量％；Ｃ１６：３〜６重量％の定性的組成を有する脂肪アルコール混合物を、ＳＯ３プラントで硫酸化した。次いで、硫酸化粗生成物を、３０％濃度のＮａＯＨ水溶液と一緒に、ステンレス製中和容器内の、重量比３：１のポリオールと水との混合物に連続的に計量添加した。中和が起こった後、最終生成物を取り出した。最終生成物は、４２重量％の硫酸化脂肪アルコール含量を有していた。ｐＨは１１であった。色は５０（ＡＰＨＡ、２０重量％濃度溶液）と測定された。 C12: 65-71 wt%; C14: 22 to 28 wt%; C16: fatty alcohol mixture having the qualitative composition of 3-6 wt%, and sulfated SO 3 plant. The crude sulfated product was then continuously metered together with a 30% strength aqueous NaOH solution into a 3: 1 weight ratio polyol and water mixture in a stainless steel neutralization vessel. The final product was removed after neutralization occurred. The final product had a sulfated fatty alcohol content of 42% by weight. The pH was 11. The color was measured as 50 (APHA, 20% strength by weight solution).

このようにして、以下の組成（全データの単位：重量％）を有する生成物（前記定性的組成の脂肪アルコール混合物に従った脂肪アルコールスルフェート）を製造した。   In this way, a product (fatty alcohol sulfate according to the qualitative composition of fatty alcohol) having the following composition (unit:% by weight of all data) was produced.

Figure 2010539262
Figure 2010539262

Claims (10)

少なくとも
（ａ）組成物の総重量に基づいて３５重量％の、一般式（Ｉ）：
Ｒ１Ｏ−ＳＯ３Ｘ （Ｉ）
［式中、Ｒ１は、６〜２２個、好ましくは１２〜１８個の炭素原子を有する、直鎖または分枝の脂肪族アルキルおよび／またはアルケニル基であり、Ｘは、アルカリ金属および／またはアルカリ土類金属、アンモニウム、アルキルアンモニウム、アルカノールアンモニウムまたはグルカンモニウムである。］
で示される１種以上の脂肪アルコールスルフェートと、
（ｂ）少なくとも１種のポリオール、および／または脂肪酸アルキルアミド、および／またはベタイン、並びに
（ｃ）水
を含んでなる組成物。 At least (a) 35% by weight, based on the total weight of the composition, of the general formula (I):
R 1 O—SO 3 X (I)
Wherein R 1 is a straight or branched aliphatic alkyl and / or alkenyl group having 6 to 22, preferably 12 to 18 carbon atoms, X is an alkali metal and / or Alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucanmonium. ]
One or more fatty alcohol sulfates represented by:
(B) A composition comprising at least one polyol and / or fatty acid alkylamide and / or betaine, and (c) water. 組成物の総重量に基づいて、３５重量％超、好ましくは３６重量％〜７０重量％、特に４０〜６０重量％、特に好ましくは４０〜５０重量％の量で脂肪アルコールスルフェートを含んでなる、請求項１に記載の組成物。   Based on the total weight of the composition, it comprises fatty alcohol sulfate in an amount of more than 35% by weight, preferably 36% to 70% by weight, in particular 40 to 60% by weight, particularly preferably 40 to 50% by weight. The composition of claim 1. グリセロール、エチレングリコール、プロピレングリコールまたはソルビトールからなる群から選択されるポリオールを含んでなり、ここで、グリセロールおよび／またはソルビトールが特に好ましい、請求項１または２に記載の組成物。   Composition according to claim 1 or 2, comprising a polyol selected from the group consisting of glycerol, ethylene glycol, propylene glycol or sorbitol, wherein glycerol and / or sorbitol are particularly preferred. 組成物の総重量に基づいて、１０〜４５重量％、好ましくは１５〜４０重量％、特に２５〜３５重量％の量で成分ｂ）を含んでなる、請求項１〜３のいずれかに記載の組成物。   4. Component b) comprising component b) in an amount of 10 to 45% by weight, preferably 15 to 40% by weight, in particular 25 to 35% by weight, based on the total weight of the composition. Composition. 組成物の総重量に基づいて、５〜４０重量％、好ましくは１０〜３０重量％、特に１５〜２５重量％の量で水を含んでなる、請求項１〜４のいずれかに記載の組成物。   Composition according to any of the preceding claims, comprising water in an amount of 5 to 40% by weight, preferably 10 to 30% by weight, in particular 15 to 25% by weight, based on the total weight of the composition. object. 組成物全体の重量に基づいて、
（ａ）３６〜４５重量％の、式（Ｉ）で示されるアルキルスルフェート、
（ｂ）２８〜４５重量％の、ポリオール、ベタイン、および／または脂肪酸アルキルアミド、
（ｃ）１０〜３４重量％の水
を含んでなる、請求項１〜５のいずれかに記載の組成物。 Based on the total weight of the composition,
(A) 36 to 45% by weight of an alkyl sulfate of formula (I),
(B) 28-45% by weight of polyols, betaines, and / or fatty acid alkylamides,
(C) The composition according to any one of claims 1 to 5, comprising 10 to 34% by weight of water. 液体または低粘性ポンプ輸送可能ペーストの状態である、請求項１〜６のいずれかに記載の組成物。   The composition according to claim 1, which is in a liquid or low-viscosity pumpable paste state. 一般式：Ｒ１−ＯＳＯ３Ｈで示される未中和アルキルスルフェートおよびアルカリを、（Ａ）水と（Ｂ）ポリオールまたは油溶性ベタインとの混合物に連続的に添加することを含む、少なくとも３５重量％の式（Ｉ）で示されるアルキルスルフェートを含んでなる請求項１に記載の製剤の製造方法であって、（Ａ）と（Ｂ）との体積比を３：１〜１：３の値に調節し、アルカリの量がアルキルスルフェートを完全に中和するのに適しており、式（Ｉ）で示される中和アルキルスルフェートの濃度が少なくとも３５重量％に達するまで、（Ａ）と（Ｂ）との混合物と、未中和アルキルスルフェートおよびアルカリとの混合を継続する、方法。 At least 35, comprising continuously adding unneutralized alkyl sulfate and alkali represented by the general formula: R 1 -OSO 3 H to a mixture of (A) water and (B) a polyol or oil-soluble betaine. The method for producing a preparation according to claim 1, comprising a weight percent of an alkyl sulfate represented by the formula (I), wherein the volume ratio of (A) to (B) is 3: 1 to 1: 3. Until the concentration of the neutralized alkyl sulfate of formula (I) reaches at least 35% by weight (A), the amount of alkali is suitable to completely neutralize the alkyl sulfate. ) And (B) and the mixing of the unneutralized alkyl sulfate and alkali continues. 洗剤または洗浄剤、或いは化粧品、例えばヘアシャンプーまたは練り歯磨きを製造するための、請求項１〜８のいずれかに記載の組成物の使用。   Use of a composition according to any of claims 1 to 8 for the manufacture of a detergent or cleaning agent or a cosmetic product, such as a hair shampoo or toothpaste. 請求項１に記載の脂肪アルコールスルフェート製剤を含んでなる、洗剤、洗浄剤、または化粧品。   A detergent, cleaning agent or cosmetic comprising the fatty alcohol sulfate formulation according to claim 1.
JP2010524384A 2007-09-14 2008-09-06 High concentration fatty alcohol sulfate composition Active JP5854605B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07018144.1 2007-09-14
EP07018144A EP2036972B1 (en) 2007-09-14 2007-09-14 Highly concentrated fatty alcohol sulphate compound
PCT/EP2008/007295 WO2009036902A1 (en) 2007-09-14 2008-09-06 Highly concentrated fatty alcohol sulfate preparation

Publications (2)

Publication Number Publication Date
JP2010539262A true JP2010539262A (en) 2010-12-16
JP5854605B2 JP5854605B2 (en) 2016-02-09

Family

ID=38921714

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2010524384A Active JP5854605B2 (en) 2007-09-14 2008-09-06 High concentration fatty alcohol sulfate composition

Country Status (11)

Country Link
US (1) US20100303739A1 (en)
EP (1) EP2036972B1 (en)
JP (1) JP5854605B2 (en)
CN (1) CN101802157B (en)
AT (1) ATE547509T1 (en)
BR (1) BRPI0816793B1 (en)
CA (1) CA2698512C (en)
ES (1) ES2383541T3 (en)
MX (1) MX302858B (en)
PL (1) PL2036972T3 (en)
WO (1) WO2009036902A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017507235A (en) * 2014-03-07 2017-03-16 エコラボ ユーエスエー インコーポレイティド Alkylamides for enhanced food soil removal and asphalt dissolution

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2833282T3 (en) 2012-04-24 2021-06-14 Stepan Co Unsaturated fatty alcohol derivatives from natural oil metathesis
WO2014072840A1 (en) 2012-11-12 2014-05-15 Galaxy Surfactants Ltd. Flowable, high active, aqueous fatty alkyl sulfates
JP6138355B2 (en) 2013-05-24 2017-05-31 ザ プロクター アンド ギャンブル カンパニー Low pH detergent composition comprising nonionic surfactant
EP3004310B1 (en) 2013-05-24 2021-07-14 The Procter & Gamble Company Low ph detergent composition
JP6271717B2 (en) 2013-05-24 2018-01-31 ザ プロクター アンド ギャンブル カンパニー Concentrated surfactant composition
CN105307624B (en) 2013-06-18 2019-12-31 株式会社Lg生活健康 Oral composition
CN107001984B (en) 2014-09-08 2019-11-12 宝洁公司 Detergent composition comprising branched surfactants
CN106715663A (en) 2014-09-08 2017-05-24 宝洁公司 Detergent compositions containing a branched surfactant
CN110648848A (en) * 2019-09-19 2020-01-03 肇庆绿宝石电子科技股份有限公司 115 ℃ large ripple current resistant aluminum electrolytic capacitor
CN115043761B (en) * 2022-07-06 2024-03-19 湖南丽臣奥威实业有限公司 Process for producing triethanolamine alkyl sulfate

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05247492A (en) * 1992-01-24 1993-09-24 Unilever Nv Detergent composition
JP2003238999A (en) * 2002-02-14 2003-08-27 Lion Corp Method for producing high concentration liquid detergent
JP2006316265A (en) * 2005-04-14 2006-11-24 Kao Corp Additive for high concentration anionic surfactant
JP2007508341A (en) * 2003-10-15 2007-04-05 ユニリーバー・ナームローゼ・ベンノートシヤープ Skin care and cleansing compositions containing oilseed products

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1818A (en) * 1840-10-10 Machine eoe
EP0693112A1 (en) * 1993-04-08 1996-01-24 The Procter & Gamble Company Secondary (2,3) alkyl sulfate surfactants in mixed surfactant particles
DE4420515A1 (en) 1994-06-13 1995-12-14 Henkel Kgaa Mild watery shaving preparations
US5536332A (en) * 1994-09-30 1996-07-16 Chun; Ho M. Shampoo composition
GB9509452D0 (en) * 1995-05-10 1995-07-05 Unilever Plc Light duty cleaning composititon
PH11997056152B1 (en) * 1996-04-16 2002-04-16 Procter & Gamble Process for the manufacture of surfactants containing branch chain alkyl groups
USH1818H (en) * 1997-10-17 1999-11-02 Sasol Technology (Proprietary) Limited Detergent and cleaning compositions derived from new detergent alcohols
DE19929511C2 (en) * 1999-06-29 2003-04-10 Cognis Deutschland Gmbh Highly concentrated flowable anionic surfactant mixtures
WO2006112492A2 (en) 2005-04-14 2006-10-26 Kao Corporation Additives for high-concentration anionic surfactants

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05247492A (en) * 1992-01-24 1993-09-24 Unilever Nv Detergent composition
JP2003238999A (en) * 2002-02-14 2003-08-27 Lion Corp Method for producing high concentration liquid detergent
JP2007508341A (en) * 2003-10-15 2007-04-05 ユニリーバー・ナームローゼ・ベンノートシヤープ Skin care and cleansing compositions containing oilseed products
JP2006316265A (en) * 2005-04-14 2006-11-24 Kao Corp Additive for high concentration anionic surfactant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017507235A (en) * 2014-03-07 2017-03-16 エコラボ ユーエスエー インコーポレイティド Alkylamides for enhanced food soil removal and asphalt dissolution

Also Published As

Publication number Publication date
JP5854605B2 (en) 2016-02-09
BRPI0816793B1 (en) 2017-05-02
CA2698512C (en) 2016-12-20
MX2010001558A (en) 2010-06-17
WO2009036902A1 (en) 2009-03-26
EP2036972B1 (en) 2012-02-29
CN101802157A (en) 2010-08-11
US20100303739A1 (en) 2010-12-02
MX302858B (en) 2012-08-30
CN101802157B (en) 2014-03-12
ES2383541T3 (en) 2012-06-22
CA2698512A1 (en) 2009-03-26
PL2036972T3 (en) 2012-07-31
ATE547509T1 (en) 2012-03-15
BRPI0816793A2 (en) 2015-03-24
EP2036972A1 (en) 2009-03-18

Similar Documents

Publication Publication Date Title
JP5854605B2 (en) High concentration fatty alcohol sulfate composition
EP3118293B1 (en) Cleaning product
EP3118294B1 (en) Cleaning product
ES2293825B1 (en) COMPOSITION CONTAINING A MONO-DI MIXTURE, AND TRIGLICERIDS AND GLYCERINE.
US8343905B2 (en) Detergent composition
EP3162881B1 (en) Cleaning product
EP3418359B1 (en) Cleaning product
JP2009540025A5 (en)
JP5923506B2 (en) Cleaning composition
EP3170886B1 (en) Cleaning product
EP3418360B1 (en) Sprayable cleaning composition
JP4342730B2 (en) Hydrotropes and skin conditioning agents for use in liquid detergent compositions
US20230119920A1 (en) Method for producing reduced glycol fatty alcohol ethoxylates, reduced glycol sulfate ethoxylated surfactants, and products
US6172035B1 (en) Preparation of thickening agents based on fatty acid monoisopropanolamide, use thereof and preparations containing same
EP3418356B1 (en) Sprayable cleaning composition

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20110901

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20130917

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20131216

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20131224

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140110

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140916

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20141215

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20150630

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150831

A911 Transfer to examiner for re-examination before appeal (zenchi)

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20150930

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20151110

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20151208

R150 Certificate of patent or registration of utility model

Ref document number: 5854605

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250